Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions – Polymer containing
Reexamination Certificate
1995-05-30
2002-01-01
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Live hair or scalp treating compositions
Polymer containing
C424S070100, C424S070110, C528S061000, C528S065000
Reexamination Certificate
active
06335003
ABSTRACT:
The present invention relates to the use of cationic polyurethanes and polyureas as ingredients of cosmetic and pharmaceutical preparations. Since some of these compounds are new, the invention further relates to these novel polyurethanes and polyureas.
Polyurethanes and polyureas which contain cationic groups through incorporation of quaternizable or protonatable tertiary amine nitrogen atoms are known. For instance, DE-A-20 19 324 (1) describes lightfast polyurethane ionomers with tertiary or quaternary ammonium nitrogen which contain structural units of the formula
in which the nitrogen atom can be quaternized or protonated. These polyurethane ionomers are recommended for a very wide range of applications, but the cosmetics and pharmaceutical sectors are not mentioned.
DE-C-11 78 586 (2) discloses polyurethanes based on polyhydroxy compounds having a molecular weight of from 400 to 10,000 and polyisocyanates wherein at least one of the components contains at least one basic tertiary amine nitrogen atom. For instance, Example 14 describes the preparation of a polyurethane from an adipic acid-hexanediol polyester, toluylene diisocyanate, 1,4-butanediol and a small amount of N-methyldiethanolamine. The polyurethane of Example 14 can be calculated to have an amine number of 27. These polyurethanes are recommended inter alia for use as hair setting agents.
In cosmetics, hair dressings, for example in the form of lotions or sprays, are used for fixing, controlling and shaping the hair. Hair dressings consist predominantly of a solution of film-forming resins or synthetic polymers. Hitherto hair dressings were chiefly based on the following film formers: shellac, homo- and copolymers of N-vinylpyrrolidone, copolymers of vinyl ethers/maleic monoesters, of (meth)acrylic acid or their esters and amides and crotonic acid with vinyl esters.
The hair dressings are applied to the hair in the form of solutions, preferably as ethanolic solutions, by spraying. The solvent evaporates to leave behind a polymer which fixes the hair strands in the desired shape at the mutual contact points. The polymer should on the one hand be sufficiently hydrophilic that it can be washed out of the hair, on the other it should be hydrophobic in order that the hair treated therewith keeps its shape, and does not become sticky, even under high atmospheric humidity.
However, the prior art polymeric film-formers such as polyvinylpyrrolidone usually have the disadvantage of excessive water absorption at elevated humidity. This property leads inter alia to an undesirable stickiness of the hair and to a loss of the hold and hence to a collapse of the hairstyle. If, on the other hand, the resistance to high humidity is improved, for example in the case of copolymers of N-vinylpyrrolidone and vinyl acetate, this jeopardizes the elasticity of the film, and the brittleness of these films can even lead to an unpleasant dusting and a flaky appearance. Moreover, it is difficult to get the hair completely clean. The abovementioned synthetic hair dressings are nonbiodegradable because of-their hydrolysis-resistant carbon-carbon chain. Shellac, by contrast, is biodegradable, but has many disadvantages. For instance, its performance characteristics as a hair dressing are worse compared with the homo- and copolymers of N-vinylpyrrolidone, especially as regards tackiness, water solubility and stiffness. Since shellac is a natural product, its properties are subject to great fluctuations.
It is an object of the present invention to provide ingredients for cosmetic and pharmaceutical preparations which are free of the above-described disadvantages of the prior art.
We have found that this object is achieved by the use of cationic polyurethanes and polyureas formed from
(a) at least one diisocyanate or reaction product thereof with one or more compounds containing two or more active hydrogen atoms per molecule, and
(b) at least one diol, primary or secondary amino alcohol, primary or secondary diamine or primary or secondary triamine each with one or more tertiary, quaternary or protonated tertiary amine nitrogen atoms
and having a glass transition temperature of at least 25° C. and an amine number of from 50 to 200, based on the non-quaternized or -protonated compounds, or other salts of these polyurethanes and polyureas, as ingredients of cosmetic and pharmaceutical preparations.
Suitable compounds of group (a) include in particular C
2
- to C
8
-alkylene diisocyanates, eg. 1,2-ethylene diisocyanate, 1,4-butylene diisocyanate, hexamethylene diisocyanate or octamethylene diisocyanate, C
5
- to C
10
-cycloalkylene diisocyanates, eg. 1,3-cyclopentylene diisocyanate, 1,3- or 1,4-cyclohexylene diisocyanate or isophorone diisocyanate, o-, m- or p-phenylene diisocyanate or (C
1
- to C
4
-alkyl) phenylene diisocyanates, eg. toluylene diisocyanate. These diisocyanates may have already been reacted with one or more compounds selected from the group consisting of diols, amino alcohols, diamines, polyesterols, polyamidediamines and polyetherols each with a number average molecular weight of up to 2000, although up to 3 mol % of the last-mentioned compounds may be replaced by triols or triamines and the diols and aminoalcohols may contain one or more tertiary, quaternary or protonated tertiary amine nitrogen atoms.
Suitable diols include for example ethylene glycol, propylene glycol, butylene glycol, neopentylglycol, polyetherols such as polyethylene glycols, polypropylene glycols or polytetrahydrofurans, block copolymers of ethylene oxide and propylene oxide or block copolymers of ethylene oxide, propylene oxide and butylene oxide in which the alkylene oxide units are present in random distribution or in the form of blocks. Preference is given to using, from the group of the diols and polyetherols, ethylene glycol, neopentylglycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol and hexaethylene glycol.
Suitable amino alcohols include for example 2-aminoethanol, 2-(N-methylamino)ethanol, 3-aminopropanol and 4-aminobutanol.
Suitable diamines include for example ethylenediamine, propylenediamine, 1,4-diaminobutane and 1,6-hexamethylenediamine and also &agr;,&ohgr;-diamines preparable by amination of polyalkylene oxides, especially polyethylene oxides with ammonia.
Suitable polyesterols include those which are customarily used for preparing polyurethanes, for example reaction products of phthalic acid and diethylene glycol, isophthalic acid and 1,4-butanediol, isophthalic acid/adipic acid and 1,6-hexanediol and also of adipic acid and ethylene glycol.
To prepare the preproducts formed from the diisocyanates and the compounds having active hydrogen atoms, it is also possible to use mixtures of these compounds, for example mixtures of a diol and a polyesterol or of a diol and polyetherols. Up to 3 mol % of said compounds in the mixtures may be replaced by triols or triamines. Suitable triols may include for example glycerol, trimethylolethane and trimethylolpropane. Suitable triamines include in particular diethylenetriamine and dipropylenetriamine.
In a preferred embodiment, the preproducts are prepared using as compounds having active hydrogen atoms at least 5 mol % of a polylactate diol of the general formula I
of a poly-&egr;-caprolactonediol of the general formula II
or of a polyamide diamine of the general formula III
in each of which
R is C
2
- to C
8
-alkylene, C
5
- to C
8
-cycloalkylene or phenylene,
R
1
and R
2
are each C
2
- to C
8
-alkylene,
R
3
is C
1
- to C
4
-alkyl, phenyl or C
7
- to C
10
-phenylalkyl, and
n and m are each from 1 to 30.
Suitable C
2
- to C
8
-alkylene for R, R
1
and R
2
includes in particular 1,2-ethylene, 1,3-propylene, 1,4-butylene and 2,2-dimethyl-1,3-propylene, but also 1,2-propylene, 1,2-butylene, 2,3-butylene, pentamethylene, hexamethylene, heptamethylene and octamethylene.
Suitable C
5
- to C
8
-cycloalkylene R includes in particular the group of the formula
but also 1,3-cyclopentylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1,4-cycloheptylene or groups of the f
Hoessel Peter
Kim Son Nguyen
Sanner Axel
Sperling-Vietmeier Karin
BASF - Aktiengesellschaft
Page Thurman K.
Seidleck Brian K.
LandOfFree
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